


Kinktober Week 2020

by Cherry_Sofa_729



Category: Sanders Sides (Web Series)
Genre: Alcohol, Anal Fingering, Anal Sex, Blowjobs, Coming In Pants, Corset, Dildos, Dirty Talk, Exhibitionism, Glory Hole, Halloween Costumes, Hemipenis, Jealousy, Kinktober 2020, Lingerie, M/M, Master/Slave, Monsterfucker, Multi, Naga!Janus, Nipple Play, Orgasm Delay/Denial, Other, Photography, Possessiveness, Riding, Sleepy Sex, Tags to be added, Threesome - M/M/M, Vibrators, Voyeurism, halloween sex, handjobs, somnophila, voyeur
Language: English
Status: Completed
Published: 2020-10-02
Updated: 2020-10-07
Packaged: 2021-03-07 18:55:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 6,887
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26762452
Author URL: https://archiveofourown.org/users/Cherry_Sofa_729/pseuds/Cherry_Sofa_729
Summary: All prompt fills for Kinktober 2020! All ships except RemRom.
Relationships: Anxiety | Virgil Sanders/Dark Creativity | Remus "The Duke" Sanders, Anxiety | Virgil Sanders/Deceit | Janus Sanders, Anxiety | Virgil Sanders/Morality | Patton Sanders/Dark Creativity | Remus “The Duke” Sanders, Creativity | Roman "Princey" Sanders/Logic | Logan Sanders, Creativity | Roman "Princey" Sanders/Logic | Logan Sanders/Morality | Patton Sanders, Dark Creativity | Remus "The Duke" Sanders/Deceit | Janus Sanders/Logic | Logan Sanders
Comments: 6
Kudos: 126





	1. Day 1

**Author's Note:**

> Prompt: Threesome. Toys under clothing. Handjob

**Notes for the Chapter:**

> Prompt: Threesome. Handjobs. Toys under clothing

“Oh… oh please… ahh.” Logan panted, withering on the cool bedsheets.   
  
His face was flushed, a contrast to the cool air of his bedroom. Though it was mid-morning, his doms had approached him with a request to do a scene. Logan thought the timing was a little inappropriate, but his dick twitched at the words, and he could never deny his doms.

Janus, on his left, was stroking his dick from root to tip with his right hand. The snake knew just how to drive him wild, squeezing near the base and thumbing over the tip. He rubbed under the head, and Logan keened. He could blow his load right there as Janus ran a sharp, pointed, bordering on painful nail under the swollen head. The pain was just as welcome as the pleasure.   
  
Before meeting Janus and Remus, Logan would’ve never thought he’d be a submissive s but his urge to please often overtook his need to be fucked. 

His balls throbbed as he tensed up, yelping as his other lover pressed another finger into his hole. 

Remus giggled wickedly, scissoring his fingers, pushing and pressing against Logan’s walls. He leaned in, letting Logan feel his hot breath on his cock before he licked around his swollen balls. 

Fondling them with his tongue, Remus pushed his fingers in further, trying to reach Logan’s prostate. He knew he’d fail to reach it, but that didn’t really matter when they had much bigger plans in store.

Logan shook with pleasure. He was so close, his dick in Janus’ grip, Remus’ hot mouth sucking on his balls. “Oh, close! Close! Please let me cum, I’m so close-“ his stomach was burning hot, shaking with the effort of not releasing till given permission. His balls were going to burst, his dick purple with need…

All of a sudden, the sensations stopped. Before he could even realize what had happened, something huge, solid and jarring was pushed into his ass. 

“What-“ he stuttered, sensations rapidly falling away, leaving him with a deep, inconsolable feeling of denial. His dick twitched angrily, not content to be left alone when he was so, so close to the edge. The ache in his gut was replaced with frustration as he thrusted up, grunting and moaning, needing just a little bit more! Just a bit, to tip him over the edge! “What are you doing?!”

“We have a meeting with the others in ten minutes.” Janus said nonchalantly, wiping his hand off and putting on his gloves. 

Remus snickered at the look on Logan’s face. “Better get your brain back in order, nerd.” 

“What-“ His dick hurt with the strain of no release. He struggled to sit up, legs spread wide around his begging cock. “You can’t leave me like this!” He growled. If they didn’t say anything he was going to start jerking off, he just couldn’t take the denial!

Janus chuckled and Remus laughed out loud. “You’re coming too. Get dressed, and no touching your dick.”

Logan couldn’t refuse a direct order, no matter how humiliated he was to be left begging his lovers for release and being forced to walk around with this  thing  stuck in his ass. 

Speaking of that.

He stood up, forcing his rock hard dick into his jeans. As he stood, though, he felt whatever was inside him slip deeper into his ass, sending him jolting up with pleasure. 

Now, now he understood. He would be getting constant pleasure with every shift he made as the dildo rubbed him oh so nicely. 

What if he came in his pants? He was already so wound up… 

The thought was somehow impossibly more arousing. He would surely pass out from the blood flowing to his dick right now. 

“Are you coming?” Janus snapped, Remus snickering at the look on Logan’s face. 

“Yes, sir.” Logan said quickly. 

————

This was torturous. Like an itch he couldn’t scratch, the dildo rubbed inside him. Much like an itch, the more it rubbed the more intense the feeling got. Soon, Logan was shifting left and right trying to scratch it, to get get something more, any more pleasure. 

“Stop shifting.” Janus hissed. “People will notice.”

Logan stood ramrod straight, not wanting to disobey an order. 

His dick twitched in his jeans. He couldn’t take much more of this without coming.   


Thinking about release only made the ache inside him more prevalent. He could sink out, disobey his doms and jerk off until he finally got some satisfaction…

But the being ordered turned him on even more, and he didn’t want to be bratty. 

Remus grinned wickedly. Little did Logan know…

He pressed a button on the remote hidden in his pocket.

Logan jolted up at the vibration running up through his ass. The pleasure rocketed through him, making his dick even harder. The dildo was snug against his prostate, making it almost impossible for Logan to stay still. 

Oh, it felt so good, so impossibly good as the toy buzzed away inside him. He had to bite his tongue and cheek to stop his moans. Ooh, nothing in the world could compare… not to this feeling of deep, satisfying relief, like eating when starving.

He had to cum, he needed it, right now. He was- he was…

_He was going to cum in front of his friends._

He couldn’t hold back anymore, couldn’t stay still. The pleasure was peaking…

A hand grabbed his and he sank out. 

————

Remus put a hand over Logan’s crotch and exhaled, getting turned on as the Logical side began to hump it erratically.

Logan’s mind was swimming with nothing but more pleasure. He whined, panted, as his balls drew up tight and his belly ached with the need to release. 

“You can cum, baby, you did so good today.” Remus allowed. 

And with another thrust, Logan came, grunting as his hips shook. The orgasm seared through his system, powerful enough to make his vision go white. 

After several long minutes, with Logan slowly humping Remus’ hand, the pleasure faded, leaving Logan exhausted and sticky. 

He went a little loopy with relief, slumping into Remus’ warm hug as the duke stopped the toy in his ass. “There we go, angel. Let’s go get you cleaned up now.”

Remus was gonna cream his jeans at just the expression Logan made while cumming. His brow furrowed, lip tucked between his teeth as he grunted. He only grunted when the orgasm was especially powerful. The flush on his cheeks as he squirmed, oh, Remus lived for it. 

Cum was rapidly drying in Logan’s jeans as they made their way to the bathroom, but he wouldn’t have it any other way. 

**Notes for the Chapter:**

> Thanks for reading and stay tuned for tomorrow’s prompt, Lingerie. Costumes. Branding.


	2. Day 2

**Summary for the Chapter:**

> Prompt: Lingerie. Costumes. Branding.

Halloween was fast approaching and the dark sides couldn’t be more excited. 

But in their excitement, Virgil had forgotten to inform Janus and Remus of a particular caveat to being accepted. 

See, on the dark side, they followed the so-called “slut rule” as outlined in the movie mean girls. The rule states that only on Halloween can a girl (or boy) dress as slutty as they want and no one can give them any shit for it. Janus and Remus (and Virgil, at one point) would simply wear some form of lingerie and animal ears and call it a “costume.”

Roman, Logan, and Patton, clearly, did not follow this rule. 

Patton was a cow. Roman was dressed as a knight, and Logan as a wizard. Virgil was dressed as Jack from the nightmare before Christmas. 

Then Remus and Janus came down. 

Janus was dressed as a “mummy,” AKA, golden lingerie with a couple scraps of dull paper to be his “wrappings.” The lingerie was gorgeous, a shiny gold star harness with chains that hit his nipples when he walked. The harness was adorned with rubies and emeralds, and left most of his scaly skin exposed, barely covered by the scrap of paper over his shoulder. 

His skirt barely covered his ass, tight like a second skin and glistening gold. The paper wrapped around his thighs, trailing down to gorgeous heeled boots. On his head was a golden tiara complete with more gemstones. His makeup was also gold, shimmering eyeshadow with huge wings of eyeliner and black lips. 

Remus, on the other hand, was dressed as a devil. 

He had morphed himself to have large, perky tits, the bottoms of which could be seen under his absolutely tiny blood red velvet crop top. Around his waist, hips, and wrapped tight around his thighs was a red harness, underneath which were tight black panties with red lace. His shoes were incredibly tall fifteen inch red platform heels, that sparkled with a coating of red glitter. Upon his unruly hair was a pair of tiny devil horns, which went nicely with his blood red eyeshadow and lips. 

Every light side in the room stopped and stared. 

“What the fuck?” Remus spoke up first. “Where’re the whores?”

Virgil slapped his own forehead. “I completely forgot to tell you guys. We don’t do the slut rule here.”

Roman looked a pouting Janus up and down hungrily. “We can do the slut rule. You look  fantastic. ” He felt his dick twitch in his pants as he saw the tip of Janus’ cock peek out from under his skirt. 

“Indeed.” Logan’s eyes were glued to Remus’ tits. “Pull that up a little, give us a show.”

Virgil wolf whistled as Remus flipped up his shirt to expose his hard nipples. “Thank god. I was worried we wouldn’t have our yearly orgy Virgie.”

Virgil rolled his eyes, getting up from the couch to observe the duke closer. He cupped a firm, perky breast and wiggled it to watch the fat jiggle and the duke squeak. 

“Yearly orgy?” Patton piped up, looking like he really wanted to tear off those bandages Janus was wearing. 

“Yeah. Halloween is a time for the devils to come out and play.” Remus shook his ass and growled seductively. 

Janus watched the demon’s ass bounce and jiggle. “We used to get together and stay up until the witching hour.” 

“Virge, you are lucky.” Roman said with a smirk. “I’d pay money to fuck Janus right now.”

Janus strolled up to his prince, giving him his best bedroom eyes. “You, my dear, get my services for free.” He grinned, pressing his dark lips to Roman’s. “If you want them.”

“Do I…”  He mumbled into the kiss. “Of course!Let’s get the night started with a graveyard smash!”

Remus cheered as he leapt into Virgil’s lap, tits bouncing as Logan moved in beside them and began to fondle his chest. 

“I wouldn’t be apposed to inviting in the nerd to fuck with us, Virgie- ahHH!” Remus cut himself off with a gasp as Virgil started licking and sucking around his nipple. “Ohh, Virgie, you know how to rock a guy’s world…”

Janus, after separating from Roman, slowly drifted towards Remus, rather upset that he wasn’t getting any attention. 

Patton blocked his path, eyes dark and hungry. “No no no baby, you’re mine tonight.”

Janus pouted a little. “But the orgy-“

“We’re gonna have our own night, kay?” Patton said sharply, eyes scanning Janus like a fax machine. He couldn’t bear to see his gorgeous baby in someone else’s arms. 

He was the jealous type, sue him. 

Roman wormed his hand up Janus’ micro-skirt and started fondling his cocks as Patton backed the snake into the couch. 

“You come down here, looking like a snaky snack and expect me to share?” Patton laughed. “Don’t forget, slut. You’re mine.”

Meanwhile, Virgil was leading Remus upstairs by his nipples, Logan hot on his heels. 

“Just look at out whore, Lo. He’s practically begging to be branded and marked.”

Remus whined, tilting his head back, exposing his neck. He wanted this MySpace cutie to bite him like this was twilight!

“My room or yours?” Logan asked, fondling Remus’ ass as he pushed the duke up the stairs. 

“Mine. I’ve got some special toys to try so I can show this devil who he belongs to. By the end of tonight, you’ll be wearing my name on your ass.” He growled, tweaking Remus’ nipple. 

Remus moaned, rushing up the rest of the stairs, dick hard and straining against his panties. 

Downstairs, Patton was having trouble. 

“Baby, how did you…” he grunted, as Janus’ skirt refused to budge past his ass. “How did you get this on?”

Roman snickered. “He’s sure got a bodacious backside. Can’t wait to feel that around my cock.”

Patton glared daggers at him. “Only I get to bless my baby with my milk.” He said, smiling deviously as he turned back to Janus. He reached up under the skirt to play with his cocks again, scraping his nails over Jan’s perineum. 

Roman groaned. “Really Pat? Cow puns? And anyway, I wanna fuck him too!”

“You’ll get your turn, baby.” Patton said offhandedly, once again struggling with Janus’ skirt. 

Janus whined, eventually giving up and slapping Patton’s hands away. He grabbed two sides of the fabric and yanked. 

The skirt spilt and fell away, revealing the bare skin underneath. 

Patton growled like an animal. “Oh, love, this cow isn’t the one getting branded tonight. Those thighs are mine.”

“Pat! Cow puns again?” Roman sounded downright offended. 

“Oh, sorry Roman, I should really get a mooooove on.”

“Patton!” 

**Notes for the Chapter:**

> Tomorrow: Master/Slave. Exhibitionism/Voyeurism


	3. Day 3

**Notes for the Chapter:**

> Prompt: Master/Slave. Exhibitionism/Voyeur

“Ohhh, Master… that feels so good, thank you…” Roman moaned, wiggling his hips as Logan pushed his tongue in deeper. After being fucked almost dry with the dildo, his tongue felt soothing and cool. 

Roman gasped as Logan pressed in as deep as he could go, flicking his tongue along his inner walls and pushing into his sweet spot. Roman’s legs fell open, exposing his drooling dick to the company in the room. 

Patton, legs and arms bound to the stiff wooden chair, whimpered as he tugged, begging to be set free and go help Roman. It wasn’t often that Patton was naughty, but when he was, he would be  _naughty._

This time, Logan had caught him fingering himself to pieces and coming over himself again and again. As punishment, Patton was restricted to a Voyeur in this scene. 

The thought of someone watching, someone begging to be in his place, only turned Roman on more. He loved putting on a show, and what was better than showing a naughty boy how well his master could treat him?

He began to thrust his hips, not satisfied with the tongue lapping at his walls. “Loooo… more!!” He begged, nudging Logan’s hand with his foot 

The other unusual part of this situation was  Patton was usually the golden boy. The obedient little angel. Roman was the brat. Roman never listened and got punishments on purpose. 

A smile grew on Logan’s face. Oh, how the tables turn. 

Patton whined, tears pickling in the corners of his eyes. He didn’t like being punished! He didn’t like feeling like the naughty one, watching Roman get off so easily!

His dick twitched as he watched Roman thrust and whine and beg. Patton was never this whiney. Patton did what he was asked and never complained. 

“You know that’s not what you call me, Princess.” Logan said sharply and Roman pouted. 

“Sorry master. Can you pretty please give me your fingers?”

Logan chuckled and pulled back, pressing a gentle kiss to Roman’s tailbone before spreading lube over his hands. 

Patton’s eyes widened. Lo- master was listening to him? That wasn’t right, that wasn’t fair! Patton never made mistakes and he was stuck in a chair, while Roman, who screwed up every other day, got to take their master’s fingers?

Roman moaned as Logan pressed his long digits right into that sweet spot. “Oooh! Thank you master!” 

“Tell me how it feels, Princess.”

“Ooh, so good… uh-“ Roman couldn’t talk, the heat inside him swirling and building as Logan pushed into him again.

“Tell our bratty Angel what I’m doing to you.”

Roman gulped, struggling to reply to the order. “He’s… uh, oh! He’s rubbing my prostate! Massaging it with those long fingers, he won’t let up and ooooohhhh it feels so good!” Roman let his head fall onto the mattress, overwhelmed by the assault to his insides. He panted and moaned, shaking with every rub to the sensitive spot.   


Logan smirked, adding another finger and slamming in harder, just how his Princess liked it. His little brat was a size queen so bad sometimes even Logan’s full cock wasn’t big enough to satisfy Roman’s urge.

Patton would do anything to be in his place right now. To be blessed with their master’s fingers. His cock was rock hard and drooling into his kakis, watching Roman become completely debauched. 

“Think you can cum just from this, Princess?” Logan growled as he watched Roman’s dick hang between his legs. 

“Mmm! Maybe! M-might take a while…”

_Let me help him!_ Patton wanted to cry out. But he shouldn’t, he said he would be master’s quiet, obedient boy. 

“W-would go a little faster if you played with my balls…” Roman said, almost as an afterthought, but Patton knew it wasn’t. Roman was always asking things of their master. Always wanting more.

Patton never wanted more than what he was given, Patton knew his role and his place as one of his master’s slaves. 

Logan chuckled, and reached his hand between Roman’s legs to do just that. Tugging on them, rolling them in his palm, Roman arched up and moaned like a fucking melody. 

And oh dear god, Patton was jealous. 

He watched, unable to take pull his eyes away, as Roman thrusted into nothing, tears of pure bliss welling up in his eyes. His voice wrecked as he continued to scream and beg in pleasure. 

“Ohh, Master…” Roman’s hands balled up in the sheets as the assault on his prostate drove him up the wall. He needed something to hold onto, he wanted to cling to Logan but his master wouldn’t like that-

“C-can you let Patton go?” He knew it was a little selfish, but he just wanted to cling to Patton for dear life as the pleasure mounted. He had to hold onto something, if Logan kept massaging him like this he’d rip the bedsheets!

“Why, Princess?”

“Oh, master, I can’t take your fingers without tearing the sheets, I need something else to clutch while you treat me so well!”

Logan thought on this for a second. “That’s a little selfish of you, Princess.”

“Well that’s what I want.” Roman pouted. “And Patton’s been a wonderful audience, so he should come play! I want him to suck me off, masTER- OH!” Logan rubbed his prostate firmly in a circle, successfully shutting up Roman and curving his face into a gorgeous O. 

“Hmm. I’ll think about it.” Logan made pointed eye contact with Patton, who was wiggling in his bonds again. 

“Please.” Patton dared to speak. “Please master, can I come play?”

Logan pushed even harder on Roman’s prostate as he made up his mind. “You can play-“ Roman let out a gorgeous sound as he clutched the sheets, thrusting back on his fingers with desperate need. “When my Princess cums untouched.”

Roman gasped, locking eyes with Patton as Logan rolled his balls in his palm again. The look in his eyes said everything Patton needed to know.  
  
Roman gave a wink and shut his eyes to concentrate on the sensations rushing through him. Patton relaxed in his chair, for he knew Roman would try his best to do it, so Patton could join.   


He smiled. Sure, he could get a little jealous, but he knew Lo would listen, and he knew Roman would never hurt him. He knew they both cared. 

**Notes for the Chapter:**

> Thanks for reading, tomorrow’s prompt is nipple play, somnophila and photography/nudes!


	4. Day 4

**Summary for the Chapter:**

> Prompt: Nipple Play. Somnophila. Photography/nudes

The morning light filtered through Logan’s windows. Like a hush had been drawn over the world, everything, even the birds, were silent. 

Logan was awake, but not up. His pillow was just so soft, his blankets heavy.

Speaking of his pillow, it breathed steadily, only hitching every few breaths. 

He was asleep on Remus’ soft supple chest. His boyfriend’s breasts were a temporary change, but a welcome one. Remus liked to shift his physical appearance and giving himself tits was just another fashion choice. He liked to fill out dresses, and obviously he liked them for sex. 

And they made a damn good pillow. 

Logan felt Remus’ breathing stutter and sharpen. 

At first, Logan tensed. A nightmare, perhaps? It was a rare occurrence, but a terrifying one. 

And yet, Remus’ body grew warm, a deep heat from his core that a simple nightmare wouldn’t supply. 

A quick roll of Remus’ hips, positioned at Logan’s lower back, confirmed Logan’s suspicions. 

Remus huffed, moving Logan’s hair. Clearly, he was having a nice dream, as he cuddled Logan closer and rolled his hips again. 

Now Logan could clearly feel the hard form of Remus’ excitement pressing against his body. He swallowed. Remus getting hard in his sleep always turned him on, something about proof of his insatiably. His boyfriend was so sex-driven he had to get pleasure even in his sleep. 

Logan, now driven by his own hardening cock, gently, oh so gently, lifted himself off of Remus and flipped around so he could look down on his lover. 

Remus shifted at the movement but didn’t wake, only bringing his hand down to rub against his cock. His breasts spread wide, nipples growing hard as he humped his own hand. 

His cheeks flushed pink, eyes flickering behind his eyelids as he was deep in REM sleep. His soft, supple lips rubbed together and parted, practically begging for a kiss. 

Logan leaned down and pecked his lips, laughing a little as drool began to run down Remus’ cheek. 

Logan’s dick ached as he watched Remus. He looked so peaceful, so at ease as he rubbed his palm against his hand, Logan wanted to savour this for the rest of time. 

He grabbed his phone, lining up his shot before snapping several gorgeous pictures of his boyfriend slowly becoming debauched. 

He sent them to Virgil with the message “I am the luckiest side.”

They had the kind of relationship where they could brag about their sex lives. 

Virgil responded with his own gorgeously dishevelled picture of Thomas, legs spread around his hard cock, with the message “figured. rem’s supplying a good dream tho. and i’m the luckiest, idiot.” 

Logan chuckled, turning back to his boyfriend. He twitched back and forth, completely unwilling to separate his hand from his cock. A gentle moan passed from his lips as he ground into his palm. 

“L-gn…” he mumbled, moaning again. 

Ah, so he was dreaming of him. That wouldn’t do, Logan decided, he wanted to have Remus wake up to his real mouth around his dick. 

He cupped Remus’ breasts, thumping over the nipples before giving them a squeeze. He rolled them both in his hands, squished them together, and made them bounce. 

Remus gave a sleepy moan but didn’t wake. Logan continued giving his rapt attention to Remus’ tits. They were just so soft, so warm, and so mesmerizing as they bounced in his hands. 

He pinched the nipple again, before sinking down low and gently moving Remus’ hand away from his crotch. 

He kept his hands gripped on Remus’ breasts as he lapped over the head of his cock. 

Remus gave a sleepy moan and nicked his hips up a little. Logan wasn’t worried about him waking up, no, he knew his boyfriend could sleep though a hurricane. 

Logan wrapped his lips around Remus’ dick and just held it there, focusing on massaging and groping Remus’ tits. 

They seemed to grow in his hands, probably Remus subconsciously wanting them bigger, until he couldn’t hold all of them. He watched, absolutely entranced, as the flesh spilled out of his hands. He pinched Remus’ nipples, before wiggling his chest, watching as ripples moved up his supple skin. 

He moved lower down on Remus’ cock, feeling it pulse in his mouth. He didn’t add suction yet, just liberally coating and licking it with his tongue, bobbing up and down as he fondled his chest. 

Remus gasped, hips stuttering up into Logan’s mouth. Logan didn’t gag, he had long ago ruined his gag reflex. 

He began to add suction, shutting his eyes to concentrate on the feel, the smell, the sound of Remus. He moaned, louder than before, as Logan breathed deep to smell the faint musty scent and squeezed his chest again.

Running his thumbs over Remus’ nipples, he swallowed him down to the root. Swallowing liberally, he hummed low in his throat to be the best vibrating fleshlight for his duke. 

Remus awoke to an absolutely delicious sensation on his groin and chest, cracking open his eyes to see Logan, bent over sucking him off while playing with his chest, hips up in the air, ass bobbing seductively. 

He moaned. “Ohhhh, thank you Logan…” he said, still a little dazed from sleep and the absolutely god-like blowjob he was receiving. 

His toes curled. “W-won’t last much longer…” he moaned, hips shaking as his balls drew up to his body, a hot coil of need tightening in his stomach. “Please, oh-“

Logan sucked harder, cheeks hollowing as he swallowed Remus down. 

With a cry and a moan, Remus came, balling his hands in the sheets and chest shaking as he quivered with the force of his orgasm. 

He flopped back on the bed. “I feel like I’m ready for another nap after that.” 

Logan chuckled and crawled his way up. He tucked himself back into his boyfriend’s side, snuggling into his soft chest. “Sorry. You just look so beautiful when you’re asleep.”

“Like I’m dead!”

“Yes, but you’re still breathing, so-“

“Like I’m dead!”

**Notes for the Chapter:**

> Tomorrow’s prompt: anal. Sleepy/morning sex. Corset.


	5. Day 5

**Summary for the Chapter:**

> Prompt: Corsets. Sleepy/Morning sex. Anal

Roman stumbled back through the door of his and Logan’s shared apartment. He had been out clubbing downtown, and was a little embarrassed to say he was a bit punch-drunk as he put his keys in the bowl by the door and toed off his red heels. 

Unlike a lot of other guys, where alcohol tended to hinder their, uh, performance, Roman after a few beers was always more riled up. 

Like now, for instance, where the whole cab ride home he was thinking, pondering, dwelling on the idea of slamming Logan into the mattress. If he had been the tiniest bit drunker he would’ve started jerking off right there in the cab. 

He breathed in deep, feeling the lacing of his tight corset dig into his chest. He loved the corset, thought it was the sexiest thing. Blood red with white lace, his boyfriend liked to call him an Angel on earth when he wore it. 

But right now, all he needed was this corset off and a dick in his ass.

He strolled upstairs, unable to wait any longer to get a good dicking. 

Opening in the door to their shared bedroom, he saw Logan, completely dead asleep, curled around his unicorn onesie. 

Roman licked his ruby-red lips. Oh the innocence just turned him on even more!

“Lo.” He said quietly, nudging his boyfriend’s shoulder. “Wake up, jamberry. I’m home.”

Logan sleepily yawned turned over, leaving the unicorn pillow in favour of rubbing his tired eyes. He struggled to sit up. “Ro?” He mumbled, half asleep. 

“Hey there love.” Roman grinned wicked. 

Logan’s tired eyes scanned his outfit. “You look good. How was the party?” 

“It was fun. But I’ve got a bit of a problem.” He said delicately. 

“What’s that?”

Roman swung his legs over Logan’s hips and rocked forward, kissing his love square on the lips, sucking a little on the bottom as he pulled away. 

“I need your cock, baby.” He whispered. 

Logan whined, sleepily fumbling with the lacing of his corset. He managed to undo the knot and started threading the laces apart.

“Couldn’t wait till morning, huh?” He muttered, yawning. 

“Sorry baby.” Roman whined, wiggling his hips back and forth. “I’m so horny, it feels like if I stop moving for two seconds I’ll explode. I need your dick.”

Logan chuckled under his breath as he got the corset loose and pulled it off Roman’s lean body. Relived that he could breathe again, Roman tossed the corset aside and leaned forward to suck and nibble at Logan’s neck. 

“Looo…” he whined, sucking a dark hickey to Logan’s neck. He thrusted forward again, rutting his cock on his thigh. 

“Okay, okay. Impatient.” Logan reached over for the bottle of lube and coated his fingers. “You’re gonna ride me, I’m too tired to actually fuck you.”

Roman didn’t really care, not with this deep starving ache inside him that needed Logan’s dick. He moaned, wiggling as Logan rimmed his asshole with a lubed finger. 

“Huh, someone had a little fun in the club bathroom.” Logan huffed, feeling how stretched Roman’s rim already was. 

“C-couldn’t take the empty feeling, needed something in me so bad I was ready to make a pit stop for a butt plug on the way home…” Roman grit his teeth and flushed beautifully as Logan pushed his fingers into him. 

Deep, oh so deep, up to his knuckle in a way that made Roman’s toes curl. 

“Oooh, Lo!” He moaned, tossing his head back. “Need your dick, please- need more, more-“ 

In response, Logan shoved in a third finger and began to scissor them roughly. Roman must’ve stretched himself out a lot back at the club, he didn’t need much prep at all.

“Logan… please!” Roman whined, practically bouncing on his fingers. “It’s not deep enough!”

“Okay okay, needy.” Logan teased, pulling off his pyjama pants and lubing up his dick. 

Roman practically salivated at the one thing he knew would satisfy his urge. He lowered himself down onto Logan’s cock with a low groan. Logan gripped the sheets, grunting as Roman took him like a champ. 

It felt so good, so satisfying, to finally have something filling the void Roman hated so much. He circled his hips, bounced a little, really appreciating the heavy cock inside him. 

“Ro- you gonna… move?” Logan said, strained with how good Roman felt around him. 

Roman yawned. It seemed now that he was filled and satisfied, he didn’t really feel like moving much. “I’m tired.”

“What? Baby, no- I’m inside you, and you still have makeup on!”

“Don’t care. Tired.” The clubbing and the long night was catching up to him. 

“Babyyy.” Logan whined, frustrated. 

“What? I was out partying all night!”

“Are you telling me the only thing that kept you awake was your insatiable appetite for my dick?”

“Yeahhhh!” Roman pouted, circling his hips again. Of course he had to crash now. He couldn’t have crashed when he came or something?

“Okay Princess. Do you wanna still get off?” 

Roman thought about it. “Yeah.” He said breathlessly, bouncing a little on Logan’s dick. 

Logan grunted, bucking up which caused Roman to tighten around him. 

This began a sort of endless feedback loop, Roman bouncing and moving back and forth, squeezing tightly whenever his prostate got hit. Which in turn made Logan buck up and push harder into his prostate. 

Roman panted breathlessly, sweat rolling down his flushed face as he rode Logan’s dick like a rodeo. Now that he was tuckered out, his only goal was cumming as soon as possible. 

Logan sympathized with that goal. A lot. 

Roman clenched around Logan like a death grip and moaned loud. “Oooh, Lo, close!” His bounces got shorter, faster, as he grabbed his own cock and jerked himself quickly. 

“Come on Princess.” Logan encouraged, and in no time at all Roman gasped, camping down on Logan as he spilt white loads of cum over his own hand. 

Logan came the second Roman squeezed him, moaning the loudest of either of them that night. 

Roman came down from his high, looked at his boyfriend and chuckled. 

Logan looked exhausted. Satisfied and happy, but exhausted. “Sleep now?” He mumbled out, barely still conscious. 

Roman yawned. “Sleep now.”

**Notes for the Chapter:**

> Tomorrow’s prompt: Toys. Teratophilia/Xenophilia. Making out


	6. Day 6

**Summary for the Chapter:**

> Prompt: Toys. Teratophilia/xenophilia. Making out

**Notes for the Chapter:**

> WOW this is short sorry I was just not up for writing much today

Why did Virgil come into the monster’s den again?

Oh right. The villagers thought he was a witch. 

Well, he was a witch, sorta. He didn’t do flashy magic but he liked making protection jars!

But no, he was always too anxious and jittery for the rest of town. Of course he would be sacrificed to the local wood monster. 

What he didn’t expect was for the monster to be so… gorgeous. 

A twelve foot long naga with a glittering golden tail, green eyes, and massive fangs, Janus (he was told to call him that) looked simply divine. Virgil unintentionally felt his cock twitch in his pants at the way the naga looked at him. 

“Oh yes, you’ll do nicely.” He said, voice oily and slick. “And they sent you so early too!”

“A-are you gonna… eat me?” Virgil asked quietly. 

He wasn’t really scared, somehow. The monster seemed… gentle, soft. Much softer than the ugly men and women in his village who laughed at him and called him names. 

“Oh no no, dearie.” Janus said with a light, gentle smile. “I’ve got a much more insatiable need than hunger right now.” He growled, and god that made Virgil hard. 

“What-“ 

Janus chuckled. “I’ve got an urge to breed, love, it is springtime after all.”

Virgil blinked, eyes widening as he understood what he meant. “Oh- breed?”

“Mate, screw, fuck, don’t care.” Janus growled, tail flicking from side to side and he surveyed Virgil. “Though I lack an attraction to both females and my own species, biology unfortunately can’t be helped and I need to make a baby.” 

He put it a little bluntly, but it was the truth. Despite his gayness, he really felt the urge to make his offspring. To help his line survive. 

“Me too.”

“What?” Virgil also had to get someone pregnant? He didn’t know humans had mating season as well…

“Not make a baby, uh, I lack attraction to females and my own species too.” 

There. Virgil admitted something he thought he would never tell a single person in the world. Something about monsters and demons just touched him in the right way. 

“Oh aren’t you just perfect. Come on dearie, kiss me.”

The monster’s scales were cool and solid beneath his hand as their lips met. The monster was clearly careful about his fangs, flipping his tongue into Virgil’s mouth. 

Kissing was nice, Virgil decided. It was better when Janus’ long tail started coiling around him. 

Soon, he was in the centre of layers and layers of his strong coils. He gave a squeeze that Virgil felt over his whole body. 

“I’m going to give you a little present, my lovely mate.” 

Virgil was maneuvered until his ass was exposed, and a slick finger pushed in. 

The fingering went quick, clearly only focused and spreading him wide. Janus spread him on his fingers, the scales rubbing against his walls in the most delicious way. 

Virgil moaned, wiggling back onto the fingers before Janus pulled out. “That’s enough.” He crooned, the end of his tail reaching behind him to grab a large dildo. 

“This is a replica of a human cock, I believe it will be easier for you to take than one or both of mine.”

Virgil only had a second to dwell on the possibility of two cocks before something solid and huge was shoved up his ass. 

He moaned, still wrapped in the coils, as Janus pumped the dildo in and out. 

“Does that feel good my mate? My dearest?”

“Yes- ooh, yes…” It felt so good, Virgil had only been fucked a couple times and nothing this deep or satisfying. The dildo slammed right into his prostate on every thrust, forcing his mouth to fall open in a beautiful moan.

“I think I’ll keep you, oh, you’re perfect. And you don’t want to go back to the human world, do you?”

“N-no… wanna stay here… be your mate forever.” 

“That’s what I like to hear. Now sit back love, and take it.”

**Notes for the Chapter:**

> Tomorrow’s prompt: boot/foot worship. Glory hole. Medical play.


	7. Day 7

**Summary for the Chapter:**

> Prompt: Glory Hole

Virgil was lonely. 

Sexually frustrated, and lonely, but the first one somehow took precedent. 

It sucked, masturbating every night to an ex he couldn’t forget. Each orgasm only made the pain and heartbreak fresh in his mind and usually had him sobbing himself to sleep. 

“How about you just go to a club?” His friend Janus suggested, sipping his red wine as they talked over the dinner Virgil was paying for. “Find someone decent to hook up with.”

“It’s not that easy.” The anxiety over strangers seeing his body was too much to pull anything like that. 

Janus sighed and pushed Virgil’s coke closer to him. He brought the straw into his mouth and lazily sucked on it. Janus peered at his lips. 

“Do you know what a glory hole is?”

So now he was here. The club wasn’t too sleazy, which was saying something for a place Janus recommended. In hindsight, a glory hole was perfect. No one had to see his body and he didn’t have to get attached to whoever sucked his dick. 

And, the club was gay, so there wasn’t a chance of someone he wasn’t attracted to sucking him off. This really was perfect. 

Still, he stuck to his booth, watching Janus dance with a couple guys who looked very happy to find a tiny blond twink like Jan. 

Virgil sunk into his hoodie. He wasn’t tiny like Jan, but he wasn’t big enough to be a bear. He really didn’t fit in here…

All these guys, wearing bandanas that had to be some kind of code… it was intimidating. 

He should head to the room. Jan gave him very explicit instructions so he wouldn’t screw up. 

Down the carpeted hallway to a tiny room. There was a hole in the wall, and… that was it. 

He shut the door and locked it, then sized up the wall in front of him. 

Virgil gulped and hesitantly knocked twice on the wall. 

A couple knocks responded. “Hey hot stuff.” Gruff voice, but high pitched. 

“Hey.” Virgil said shakily. “Uh, it’s my first time doing something like this, so-“

“That’s fine. Stick it through, I’ve come here for dick, I want dick.”

Rude. Virgil thought, but accurate. “What are your pronouns?”

”He/Him. You?”

”Same.” At least now he knew how to refer to the man putting his mouth on his cock. 

He fumbled with his belt and tugged his pants down, before pulling his dick out of his pants. He hesitated.

What if this guy was creepy? What if he had a mouth STI? Did mouth STI’s even exist?

“What’s up, Virgin.” The man said, after more than a couple seconds of blank silence.

Oh god that’s close to his actual name. “I’m just nervous.”

“Well, honey. It’s okay. I’m not gonna bite your dick off. Want me to walk you through what I’m gonna do?”

“Y-yeah…” that was awfully nice of him. Maybe this dude wasn’t a creep.

“Okay. Just put it through, angel.”

Virgil held the base of his dick as he put it through the hole, meeting the cool air on the other side.

There. The freakiest part was over.

“Okay sweet cheeks. Damn, your cock is pretty. Even while soft.” 

A rough finger ran down his dick, making Virgil shiver. The man gently wrapped his hand around it and stroked slowly. 

“How big are you, sugar?”

Virgil shuttered at the pleasure running up through his body as the man stroked him. “E-eight inches.”

“Ooh, nice and big.” Virgil whimpered at that. 

The man picked up the pace, stroking him faster with a solid grip. His hand was a little wet, maybe they got lube on the other side. It felt incredibly good, his anxiety disappearing under a haze of lust. 

“Would you like me to suck you off now, gorgeous?”

“Y-yeah…”

He felt something warm and wet come over the top part of his cock and slowly sink down. The pleasure built as he sank lower and lower until he heard the gentle thud of the man’s head hitting the wall. 

Something tickled the end of his dick. “Do you have a moustache?”

The man hummed a yes, making Virgil’s knees quake, and started to increase the suction as he pulled back and pushed forward. 

God this felt good. Everything surged through his system so fast after so long with no intimate contact. He braced his palm flat against the wall as he moaned, subconsciously rocking his hips to try and get more stimulation. 

The man pulled off for a moment. “That’s it, sugar. Come for me.”

Virgil’s toes curled in his doc martens as he came into a strangers mouth. 

It was damn good orgasm. His best in a long time. He was never loud in bed, but he couldn’t contain the moan he released when the man sunk back down and sucked like he was trying to take out snake venom.

When he recovered, tucking his dick back into his pants and redoing his belt, a piece of paper was pushed through the hole. 

_Hey sugar. My name’s Remus and you sound pretty cute so I thought I’d shoot my shot. Wanna hang out some time?_

And a number. Virgil smiled and tucked the paper into his pocket. Tonight had been a better idea than he thought. 

**Notes for the Chapter:**

> Tomorrow’s prompt: double penetration. Begging. Degradation.


End file.
